Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 108 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2Luxury Catamaran Whale Watch
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More
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                  Likely to Sell Out                  Luxury Catamaran Whale Watch
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                      Hawaii
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                                            Superb40 reviews5
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More
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                  Likely to Sell Out                  Afternoon Sail & Snorkel to the Captain Cook Monument
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                      Hawaii
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                                            Superb702 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
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                  Likely to Sell Out                  Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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                      Hawaii
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                                            Superb259 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
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                  Likely to Sell Out                  Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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                      Hawaii
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                                            Superb807 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
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                  Likely to Sell Out                  Waikiki Sunset Boat Cruise
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                      Hawaii
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                                            Superb64 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More
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                  Likely to Sell Out                  Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
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                      Hawaii
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                                            Superb178 reviews5
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
2-Hour Oahu Sunset Catamaran Sail
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More
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                  Likely to Sell Out                  2-Hour Oahu Sunset Catamaran Sail
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                      Hawaii
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                                            Superb112 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More
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                  Likely to Sell Out                  Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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                      Hawaii
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                                            Superb150 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More
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                  Likely to Sell Out                  Deluxe Sail & Snorkel to the Captain Cook Monument
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                      Hawaii
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                                            Superb464 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....
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                      Likely to Sell Out                      
                  Kona Tradewind Catamaran Day Sail
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More
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                  Likely to Sell Out                  Kona Tradewind Catamaran Day Sail
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                      Hawaii
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                                            Superb40 reviews4.8
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....
Free Cancellation
(Saving 16% )
Sunset Cocktail Cruise from Anaeho'omalu Bay
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More
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                  Likely to Sell Out                  Sunset Cocktail Cruise from Anaeho'omalu Bay
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                      Hawaii
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                                            Superb60 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More
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                  Likely to Sell Out                  Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
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                      Hawaii
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                                            Superb675 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More
 Likely to Sell Out
                  
                  Likely to Sell Out                  Afternoon Sail & Snorkel to the Captain Cook Monument
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                      Hawaii
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                                            Superb245 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More
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                  Likely to Sell Out                  Sunset and Manta Ray Snorkel Adventure
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                      Hawaii
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                                            Superb812 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More
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                  Likely to Sell Out                  Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
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                      Hawaii
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                                            Superb147 reviews4.7
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More
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                  Likely to Sell Out                  Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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                      Hawaii
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                                            Superb154 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More
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                  Likely to Sell Out                  Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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                      Hawaii
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                                            Superb928 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More
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                  Likely to Sell Out                  Half-Day Deluxe Molokini Snorkel Excursion in Maui
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                      Hawaii
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                                            Superb94 reviews4.9
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....
Waikoloa Catamaran Snorkel Sail Including Lunch
Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snorkeling cruise. As you head out across the clear Pacific waters, enjoy panoramic views of volcanic mountains, golden coastline, and ... More
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                  Likely to Sell Out                  Waikoloa Catamaran Snorkel Sail Including Lunch
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                      Hawaii
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                                            Superb98 reviews4.6
Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snork....
Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More
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                  Likely to Sell Out                  Snorkel with Manta Rays Guaranteed
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                      Hawaii
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                                            Superb733 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
